Flight inspiration
Where to fly cheap from Chicago (ORD)
Rank the cheapest cached destinations anywhere out of Chicago, grouped by budget. Find inspiration here, then search your exact dates for current availability.
Cheapest escapes from Chicago
Destinations by budget
Under $100: 19 cached destinations.
$100–$200: 1 cached destination.
Full cheapest ranking
| Route | Fare snapshot | Stops | Departure | Action |
|---|---|---|---|---|
| ORD → MSPAA | $51.00 | Nonstop | Oct 25, 2026 | Search |
| ORD → BRLLF | $54.00 | Nonstop | Oct 15, 2026 | Search |
| ORD → FLLF9 | $55.00 | Nonstop | Oct 6, 2026 | Search |
| ORD → STLAA | $56.00 | Nonstop | Oct 30, 2026 | Search |
| ORD → CLEAA | $57.00 | Nonstop | Oct 21, 2026 | Search |
| ORD → PHLF9 | $59.00 | Nonstop | Oct 29, 2026 | Search |
| ORD → MCOF9 | $66.00 | Nonstop | Mar 3, 2027 | Search |
| ORD → LAXF9 | $74.00 | Nonstop | Oct 22, 2026 | Search |
Data retrieved Sep 25, 2026. This is cached planning data, not a guaranteed quote.